101555-60-6

Basic information

• Product Name: BOC-D-BETA-HOMOPROLINE
• Synonyms: RARECHEM AK PT F109;(R)-2-CARBOXYMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;BOC-D-BETA-HOMOPROLINE;Boc-D-b-HoPro-OH;(R)-2-(Carboxymethyl)pyrrolidinium chloride;(R)-Pyrrolidine-2-acetic acid hydrochloride;(R)-2-(1-(tert-butoxycarbonyl)pyrrolidin-2-yl)acetic acid;Boc-D-beta-HoPro-OH
• CAS NO: 101555-60-6
• Molecular Formula: C₁₁H₁₉NO₄
• Molecular Weight: 165.62
• Product Categories: Beta amino acids
• Mol File: 101555-60-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 303°C at 760 mmHg
• Flash Point: 137.1°C
• Appearance: /
• Density: 1.151±0.06 g/cm3(Predicted)
• Vapor Pressure: 0.000221mmHg at 25°C
• Storage Temp.: 2-8°C
• PKA: 4.56±0.10(Predicted)
• CAS DataBase Reference: BOC-D-BETA-HOMOPROLINE(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-D-BETA-HOMOPROLINE(101555-60-6)
• EPA Substance Registry System: BOC-D-BETA-HOMOPROLINE(101555-60-6)

Safety Data

• Hazardous Substances Data: 101555-60-6(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white solid

InChI:InChI=1/C6H11NO2.ClH/c8-6(9)4-5-2-1-3-7-5;/h5,7H,1-4H2,(H,8,9);1H/t5-;/m1./s1

Upstream product

• 201039-13-6 (R)-2-cyanomethyl pyrrolidine-1-carboxylic acid, tert-butyl ester 
• 128510-88-3 tert-butyl (R)-2-(4-methylbenzenesulfonyloxymethyl)pyrrolidine-1-carboxylate 
• 59378-81-3 1-(tert-butoxycarbonyl)prolin-2R-ol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 61350-65-0 (R)-2-(pyrrolidin-2-yl)acetic acid 
• 118758-56-8 tert-butyl 2-(2-ethoxy-2-oxoethyl)pyrrolidine-1-carboxylate 
• 439918-59-9 (R)-2-(pyrrolidin-2-yl)acetic acid hydrochloride salt 
• 152665-79-7 (R)-tert-butyl 2-(2-diazoacetyl)pyrrolidine-1-carboxylate 
• 37784-17-1 N-(tert-butoxycarbonyl)-D-proline 

Downstream Products

• 1314696-17-7 tert-butyl (2R)-2-(2-[4-(2-methoxyphenyl)piperazin-1-yl]-2-oxoethyl)pyrrolidine-1-carboxylate 
• 1314696-19-9 tert-butyl (2R)-2-(2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl)pyrrolidine-1-carboxylate 
• 1314696-20-2 1-(2-((2R)-1-[(4-fluorophenyl)sulfonyl]pyrrolidin-2-yl)ethyl)-4-methylpiperidine 
• 1314696-21-3 1-(2-((2R)-1-[(2-fluorophenyl)sulfonyl]pyrrolidin-2-yl)ethyl)-4-methylpiperidine 
• 1314696-23-5 4-methyl-1-(2-((2R)-1-[(4-nitrophenyl)sulfonyl]pyrrolidin-2-yl)ethyl)piperidine 
• 1314696-26-8 4-methyl-1-(2-((2R)-1-[(2-nitrophenyl)sulfonyl]pyrrolidin-2-yl)ethyl)piperidine 
• 1314696-28-0 1-(2-((2R)-1-[(4-fluorophenyl)sulfonyl]pyrrolidin-2-yl)ethyl)-4-(2-methoxyphenyl)piperazine 
• 1314696-32-6 1-(2-((2R)-1-[(2-fluorophenyl)sulfonyl]pyrrolidin-2-yl)ethyl)-4-(2-methoxyphenyl)piperazine 
• 1314696-33-7 1-(2-methoxyphenyl)-4-(2-((2R)-1-[(4-nitrophenyl)sulfonyl]pyrrolidin-2-yl)ethyl)piperazine 
• 1314696-35-9 1-(2-methoxyphenyl)-4-(2-((2R)-1-[(2-nitrophenyl)sulfonyl]pyrrolidin-2-yl)ethyl)piperazine 
• 1314696-36-0 1-(2-((2R)-1-[(4-[⁽¹⁸⁾F]-fluorophenyl)sulfonyl]pyrrolidin-2-yl)ethyl)-4-methylpiperidine 
• 1314696-37-1 1-(2-((2R)-1-[(2-[⁽¹⁸⁾F]-fluorophenyl)sulfonyl]pyrrolidin-2-yl)ethyl)-4-methylpiperidine 
• 1314696-40-6 1-(2-((2R)-1-[(4-[⁽¹⁹⁾F]-fluorophenyl)sulfonyl]pyrrolidin-2-yl)ethyl)-4-(2-methoxyphenyl)piperazine 
• 1314696-41-7 1-(2-((2R)-1-[(2-[⁽¹⁹⁾F]-fluorophenyl)sulfonyl]pyrrolidin-2-yl)ethyl)-4-(2-methoxyphenyl)piperazine 

Relevant articles and documents

Enzymatic resolution of cyclic N-Boc protected β-aminoacids

Methyl and ethyl esters of N-Boc homoproline, homopipecolic acid and 3-carboxymethyl-morpholine were kinetically resolved by hydrolysis catalysed by Burkholderia cepacia lipase to give the corresponding acids and residual esters in enantiomeric excesses better than 99% (E > 100).

Synthesis and biological evaluation of potential 5-HT7 receptor PET radiotracers

Brain serotonin 7 receptor (5-HT7) is involved in several mood disorders and drug candidates targeting this subtype are currently in development. Positron emission tomography (PET) is a molecular imaging modality offering great promise for accelerating the process from preclinical discovery to clinical phases. As no PET radiopharmaceutical has yet been used successfully to study the 5-HT7 receptor in vivo, our objective is to develop the first 5-HT7 fluorine-18 labeled radiotracer. Four structural analogs of SB269970, a specific 5-HT7 receptor antagonist, divided in FP3 series and FPMP series were synthesized. Their antagonist effects were investigated by cellular functional assay. Nitro-precursors of these analogs were radiolabeled via a [18F-]nucleophilic substitution and in vitro autoradiographies were performed in rat brain. Chemical and radiochemical purities of fluorine radiotracers were >99% with specific activities in 40-129 GBq/μmole range. The four derivates presented antagonism potencies toward 5-HT7 receptors (pKB) between 7.8 and 8.8. The four PET radiotracers had suitable characteristic for 5-HT7 receptor probing in vitro even if the FP3 series seemed to be more specific for this receptor. These results encourage us to pursue in vivo studies.

Endomorphin-1 analogues containing β-proline are μ-opioid receptor agonists and display enhanced enzymatic hydrolysis resistance

In this paper we describe the synthesis and affinity toward the μ-opioid receptor of some tetrapeptides obtained from endomorphin-1, H-Tyr-Pro-Trp-Phe-NH2 (1), by substituting each amino acid in turn with its homologue. The ability to bind μ -opioid receptors depends on the β-amino acid, and in particular 4, which contains β-L-Pro, has a KI, in the nanomolar range. The peptides 4 and 5 are significantly more resistant to enzymatic hydrolysis than 1. The same compounds, as well as the μ-opioid receptor agonist DAMGO, produced a concentration-dependent inhibition of forskolin-stimulated cyclic AMP formation, thus behaving as μ-opioid agonists. These features suggest that this novel class of endomorphin-1 analogues may represent suitable candidates for the in vivo investigation as potential μ-opioid receptor agonists.